Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 24, Pages 7199-7207Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201000149
Keywords
alcohols; alkylation; amines; heterogeneous catalysis; hydrogen; ruthenium
Categories
Funding
- Japan Science and Technology Agency (JST)
- Global COE Program
- Ministry of Education, Culture, Sports, Science and Technology
- Grants-in-Aid for Scientific Research [21360391] Funding Source: KAKEN
Ask authors/readers for more resources
The N-alkylation of ammonia (or its surrogates, such as urea, NH4HCO3, and (NH4)(2)CO3) and amines with alcohols, including primary and secondary alcohols, was efficiently promoted under anaerobic conditions by the easily prepared and inexpensive supported ruthenium hydroxide catalyst Ru(OH)(x)/TiO2. Various types of symmetrically and unsymmetrically substituted tertiary amines could be synthesized by the N-alkylation of ammonia (or its surrogates) and amines with primary alcohols. On the other hand, the N-alkylation of ammonia surrogates (i.e., urea and NH4HCO3) with secondary alcohols selectively produced the corresponding symmetrically substituted secondary amines, even in the presence of excess amounts of alcohols, which is likely due to the steric hindrance of the secondary alcohols and/or secondary amines produced. Under aerobic conditions, nitrites could be synthesized directly from alcohols and ammonia surrogates. The observed catalysis for the present N-alkylation reactions was intrinsically heterogeneous, and the retrieved catalyst could be reused without any significant loss of catalytic performance. The present catalytic transformation would proceed through consecutive N-alkylation reactions, in which alcohols act as alkylating reagents. On the basis of deuterium-labeling experiments, the formation of the ruthenium dihydride species is suggested during the N-alkylation reactions.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available